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Quantification of the emetic toxin cereulide in food products by LC-MS using synthetic cereulide as a standard

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Abstract
Bacillus cereus produces the emetic toxin cereulide, a cyclic dodecadepsipeptide that can act as a K+ ionophore, dissipating the transmembrane potential in mitochondria of eukaryotic cells. Because pure cereulide has not been commercially available, cereulide content in food samples has been expressed in valinomycin equivalents, a highly similar cyclic potassium ionophore that is commercially available. This research tested the biological activity of synthetic cereulide and validated its use as a standard in the quantification of cereulide contents in food samples. The synthesis route consists of 10 steps that result in a high yield of synthetic cereulide that showed biological activity in the HEp-2 cell assay and the boar sperm motility assay. The activity is different in both methods, which may be attributed to differences in K+ content of the test media used. Using cereulide or valinomycin as a standard to quantify cereulide based on liquid chromatography-mass spectrometry (LC-MS), the concentration determined with cereulide as a standard was on average 89.9% of the concentration determined using valinomycin as a standard. The recovery experiments using cereulide-spiked food products and acetonitrile as extraction solute showed that the LC-MS method with cereulide as a standard is a reliable and accurate method to quantify cereulide in food, because the recovery rate was close to 100% over a wide concentration range.
Keywords
VALINOMYCIN, DODECADEPSIPEPTIDE, ASSAY, BACILLUS-CEREUS

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Chicago
Biesta-Peters, Elisabeth G, Martine W Reij, Richard H Blaauw, Paul H in  ’t Veld, Andreja Rajkovic, Monika Ehling-Schulz, and Tjakko Abee. 2010. “Quantification of the Emetic Toxin Cereulide in Food Products by LC-MS Using Synthetic Cereulide as a Standard.” Applied and Environmental Microbiology 76 (22): 7466–7472.
APA
Biesta-Peters, E. G., Reij, M. W., Blaauw, R. H., in  ’t Veld, P. H., Rajkovic, A., Ehling-Schulz, M., & Abee, T. (2010). Quantification of the emetic toxin cereulide in food products by LC-MS using synthetic cereulide as a standard. APPLIED AND ENVIRONMENTAL MICROBIOLOGY, 76(22), 7466–7472.
Vancouver
1.
Biesta-Peters EG, Reij MW, Blaauw RH, in  ’t Veld PH, Rajkovic A, Ehling-Schulz M, et al. Quantification of the emetic toxin cereulide in food products by LC-MS using synthetic cereulide as a standard. APPLIED AND ENVIRONMENTAL MICROBIOLOGY. 2010;76(22):7466–72.
MLA
Biesta-Peters, Elisabeth G, Martine W Reij, Richard H Blaauw, et al. “Quantification of the Emetic Toxin Cereulide in Food Products by LC-MS Using Synthetic Cereulide as a Standard.” APPLIED AND ENVIRONMENTAL MICROBIOLOGY 76.22 (2010): 7466–7472. Print.
@article{1173790,
  abstract     = {Bacillus cereus produces the emetic toxin cereulide, a cyclic dodecadepsipeptide that can act as a K+ ionophore, dissipating the transmembrane potential in mitochondria of eukaryotic cells. Because pure cereulide has not been commercially available, cereulide content in food samples has been expressed in valinomycin equivalents, a highly similar cyclic potassium ionophore that is commercially available. This research tested the biological activity of synthetic cereulide and validated its use as a standard in the quantification of cereulide contents in food samples. The synthesis route consists of 10 steps that result in a high yield of synthetic cereulide that showed biological activity in the HEp-2 cell assay and the boar sperm motility assay. The activity is different in both methods, which may be attributed to differences in K+ content of the test media used. Using cereulide or valinomycin as a standard to quantify cereulide based on liquid chromatography-mass spectrometry (LC-MS), the concentration determined with cereulide as a standard was on average 89.9% of the concentration determined using valinomycin as a standard. The recovery experiments using cereulide-spiked food products and acetonitrile as extraction solute showed that the LC-MS method with cereulide as a standard is a reliable and accurate method to quantify cereulide in food, because the recovery rate was close to 100% over a wide concentration range.},
  author       = {Biesta-Peters, Elisabeth G and Reij, Martine W and Blaauw, Richard H and in 't Veld, Paul H and Rajkovic, Andreja and Ehling-Schulz, Monika and Abee, Tjakko},
  issn         = {0099-2240},
  journal      = {APPLIED AND ENVIRONMENTAL MICROBIOLOGY},
  keywords     = {VALINOMYCIN,DODECADEPSIPEPTIDE,ASSAY,BACILLUS-CEREUS},
  language     = {eng},
  number       = {22},
  pages        = {7466--7472},
  title        = {Quantification of the emetic toxin cereulide in food products by LC-MS using synthetic cereulide as a standard},
  url          = {http://dx.doi.org/10.1128/AEM.01659-10},
  volume       = {76},
  year         = {2010},
}

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